AU594796B2 - Primer for cycloolefin polymer articles - Google Patents
Primer for cycloolefin polymer articles Download PDFInfo
- Publication number
- AU594796B2 AU594796B2 AU75543/87A AU7554387A AU594796B2 AU 594796 B2 AU594796 B2 AU 594796B2 AU 75543/87 A AU75543/87 A AU 75543/87A AU 7554387 A AU7554387 A AU 7554387A AU 594796 B2 AU594796 B2 AU 594796B2
- Authority
- AU
- Australia
- Prior art keywords
- composition
- cycloolefin polymer
- cellulose ester
- primer
- primer coating
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 229920000089 Cyclic olefin copolymer Polymers 0.000 title claims description 22
- 239000000203 mixture Substances 0.000 claims description 44
- 239000002987 primer (paints) Substances 0.000 claims description 42
- 229920002678 cellulose Polymers 0.000 claims description 15
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 claims description 14
- 229920001807 Urea-formaldehyde Polymers 0.000 claims description 11
- 229920000180 alkyd Polymers 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 10
- 229910052782 aluminium Inorganic materials 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 239000003377 acid catalyst Substances 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 8
- 239000004411 aluminium Substances 0.000 claims description 8
- 239000000049 pigment Substances 0.000 claims description 8
- -1 poly(dicyclopentadiene) Polymers 0.000 claims description 8
- 238000010186 staining Methods 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 239000000020 Nitrocellulose Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229920001220 nitrocellulos Polymers 0.000 claims description 5
- 238000010422 painting Methods 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 description 7
- 230000003078 antioxidant effect Effects 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 238000013508 migration Methods 0.000 description 4
- 230000005012 migration Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 210000003298 dental enamel Anatomy 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/08—Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/0427—Coating with only one layer of a composition containing a polymer binder
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2365/00—Characterised by the use of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Paints Or Removers (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
Description
JI.
:I
594796 S F Ref: 26852 FORM COMMONWEALTH OF AUSTRALIA PATENTS ACT 1952 COMPLETE SPECIFICATION
(ORIGINAL)
FOR OFFICE USE: Class Int Class Complete Specification Lodged: Accepted: Published: Priority: Related Art: This ocument contains the amendments made utider Section 49 and is correct for r, iAting.
Name and Address of Applicant: Address for Service: Hercules Incorporated Hercules Plaza Nilmington Delaware 19894 UNITED STATES OF AMERICA Spruson Ferguson, Patent Attorneys Level 33 St Martins Tower, 31 Market Street Sydney, New South Wales, 2000, Australia Complete Specification for the invention entitled: PRIMER COATING FOR CYCLOOLEFIN POLYMER ARTICLES The following statement is a full description of this invention, including the best method of performing it known to me/us 1 I r' 1 5845/10 Kt i Lt f t w LS ~hl 99 99 *0 9 .9,9 999, .9 9 9 *9 9 9*9 9 .9 9 *e.
*9 0475p Kraus Case 1 PRIMER COATING FOR CYCLOOLEFIN POLYMER ARTICLES Abstract of the Disclosure Disclosed is a primer coating for cycloolefin polymer articles comprising an alkyd resin, a urea-formaldehyde resin, at least one 2-4 carbon alkanol, a nonleafing aluminum pigment and an acid catalyst. A cellulose ester and a solvent for the cellulose ester may also be included. The primer coating prevents migration of antioxidant from the cycloolefin polymer into a subsequently applied topcoat.
It 9
~I
jr i rv 1
A-J
A This invention relates to a primer coating composition for molded articles made from cycloolefin polymers. This invention especially relates to a crosslinkable, alcohol-based primer coating composition that is used to prevent staining of the topcoat that is subsequently applied to the molded article.
Molded articles made from cycloolefin polymers such as thermoset poly(dicyclopentadiene), the preparation of which is described in U.S.P.
4,400,340, are typically painted with a topcoat such as a white acrylicurethane enamel. It has been found that a brown stain, attributed to the antioxidant used in the polymer, migrates through the paint film. The antioxidant stain discolors the painted article and is objectionable for cosmetic reasons.
It has now been found that a crosslinkable primer coating composition having a solvent systesm that is a nonsolvent for cycloolefin polymers and containing a nonleafing aluminium pigment, will prevent staining of a topcoat subsequently applied to a cycloolefin polymer article.
The invention provides a primer coating composition for cycloolefin polymer articles comprising from about 8% to about 46% alkyd resin, (b) from about 3% to about 18% urea-formaldehyde resin, from about 25% to 20 about 83% of at least one 2-4 carbon alkanol, from about 1.5% to about 24% nonleafing aluminium pigment, from about 0.5% to about 3.5% acid catalyst, based on the total weight of the composition,.
The invention also provides a process for preventing staining of painted cycloolefin polymer articles comprising applying a primer coating composition to the articles before painting, said composition comprising: from about 8% to about 46% alkyd resin; from about 3% to about 18% urea-formaldehyde resin; from about 25% to about 83% of at least one 2-4 carbon alkanol; from about 1.5% to about 24% of nonleafing aluminium pigment; and from about 0.5% to about 3.5% of an acid catalyst, based on the total weight of the composition and then causing the t C f composition to cross-link before painting.
The primer coating composition of this invention is 71 V& 7 -il: c I~ o applied to molded articles made from cycloolefin polymers.
Typical of such cycloolefin polymers is thermoset poly(dicyclopentadiene). Without the primer, the preferred antioxidant typically used in cycloolefin polymers, N,N'-diphenyl-pphenylenediamine, migrates into a subsequently applied topcoat and causes staining of the paint film.
Three factors contribute to the success of the primer coating composition of this invention in preventing the migration of the antioxidant into a subsequently applied topcoat.
The first factor is the use of at least one 2-4 C monohydric Salkanol as the solvent system for the primer coating composi- *e tion. Aromatic and aliphatic hydrocarbon solvents, esters and ketones soften cycloolefin polymers and would allow the antioxidant stain to migrate freely. The alkanol has no pronounced effect on cycloolefin polymers and thereby helps to eliminate stain formation. The preferred solvent system for the primer coating composition is a mixture of from about 21% to about 83% anhydrous ethanol and from about 4% to about 17% butanol.
c* 20 The second factor is the use of a nonleafing aluminum V c pigment. Such pigment particles orient themselves within the primer coating film in an overlapping fashion and act as a barrier against stain migration.
The third factor is the use of a crosslinkable filmforming system for the primer coating composition. The crosslinked film acts as a further barrier against stain migration.
One component of the film-former is an alkyd resin. Any alkyd resin that is soluble in the alkanol solvent and crosslinks rapidly in the presence of an acid catalyst can be used. The alkyd resin is present in an amount of from about 8% to about 46%, based on the total weight of the primer composition. The second component of the film-former is a urea-formaldehyde resin. Any urea-formaldehyde resin that is soluble in the alkanol solvent and crosslinks rapidly in the presence of an acid catalyst can be used. The urea-formaldehyde resin is present in an amount of from about 3% to about 18%, based on :i ~1
I
ii w j K i A i -c r isi (i"i i g,,arr the total weight of the primer composition. The film-former may also comprise a cellulose ester such as nitrocellulose or cellulose acetate butyrate to increase the drying rate of the primer composition. Any cellulose ester that is soluble in a combination of the alkanol and a solvent for the cellulose ester can be used. Nitrocellulose having an average nitrogen content of about 11% is preferred. When the cellulose ester is used it is present in an amount of from about 2% to about 22%, based on the total weight of the composition. When a cellulose ester is present in the composition, the composition 0 also includes from about 2.5% to about 11%, based on the total weight of the composition, of a solvent for the cellulose ester, ethyl acetate. Other esters, and ketones such as I* methyl ethyl ketone can also be used as the solvent for the S"'.15 cellulose ester.
too The primer coating composition also comprises an acid catalyst that is capable of initiating crosslinking between the alkyd resin and the urea-formaldehyde resin at ambient temperature. Suitable catalysts include, but are not limited e' ,20 to, methanesulfonic acid, phenyl acid phosphate and paratoluenesulfonic acid. Para-toluenesulfonic acid is preferred.
c The acid catalyst is present in an amount of from about to about based on the total weight of the primer coating.
c, r2 25 The primer coating composition can be applied to the cy- ,cc, cloolefin polymer article by any method commonly used in the art including brushing, dipping and spraying. Spraying is preferred for cosmetic reasons. The primer coating will crosslink overnight at ambient temperature, or it can be air dried for a short period of time, 15 minutes, and then baked at a temperature not exceeding 75*C.
In this specification all parts and percentages are by weight unless otherwise noted. The following examples are illustrative of this invention and are not intended to limit its scope in any way.
k.
2, i; Iw i i i i I IL :T:i 1 i ig! sil ar~ 4 Example 1 A primer coating composition designated as Primer A having the following composition is prepared: Nitrocellulose (1) Alkyd resin (2) Urea-formaldehyde resin (3) Anhydrous ethanol Butanol Ethyl acetate Nonleafing aluminium paste (4) Para-toluenesulfonic acid in isopropanol Parts by Weight 8.66 24.63 6.94 41.54 8.49 5.48 2.90 P1.36 100.0
I
94 .9 Ii Another suitable primer coating composition designated as Primer B having the following composition is prepared: Alkyd resin (2) Urea-formaldehyde resin (3) Anhydrous ethanol Butanol Nonleafing aluminium paste (4) Para-toluenesulfonic acid in isopropanol Parts by Weight 45.14 13.58 32.06 4.25 4.15 100.0 100.0 SS Grade 1/4 sec, isopropyl alcohol-wet, manufactured by Hercules Inc and is a registered trade mark.
,tcs. K-1600-70A polyester resin manufactured by McCloskey Corp and is a registered trade mark.
Beetle 60, a fast cure methylated urea-formaldehyde resin manufactured by American Cyanamid Co and is a registered trade mark.
Lansford-243 nonleafing aluminium paste manufactured by Silberline Mfg. Co. and is a registered trade mark 0' 1> ki nI:~: 41l V
C
,nn u 07l I Ten panels molded from poly(dicyclopentadiene) containing N,N'-diphenyl-p-phenylenediamine antioxidant are preparod for test purposes. Four panels are coated with primer A and topcoated with IMRON acrylic-urethane white enamel manufactured by DuPont and is a registered trade mark. Four panels are coated with Primer B and topcoated with IMRON. Two panels are coated with IMRON only. The finishing schedule for the primer coating and enamel topcoat is as follows: 1. Spray apply a primer coating that is 4-5 mils thick when wet.
2. Air dry 15 minutes.
3. Bake 20 minutes at 71 0
C.
4. Spray apply a coating of IMRON that is 4-5 mils thick when wet.
Air dry 15 minutes.
6. Bake 20 minutes at 71 0
C.
The stain resistance of the painted panels is determined in the following manner. Tristimulis values of L and b are recorded with a Hunter Lab Colorimeter. The L number is a measurement of whiteness and the b Svalue is a measure of yellowing. Lower values of b are more desirable than higher values, and minus values are more desirable than plus values. The highest values of L are the most desirable. The panels are then baked at 105 0 C and L and b values are recorded after 7 days and 18 days. The readings are given in the table below.
t c
SC
V Ct CC ii ir
.I
rr" I -ci; ;:ji i, Ar:; 7, -6- Sample No._ 1 Primer A/IMRON 2 Primer A/IMRON 3 Primer A/IMP.ON 4 -Primer A/IMRON Primer B/IMRON 6 Primer B/IMRON 7 Primer B/IMRON 8 Primer B/IMRON 9 IMRON topcoat only 10 IMRON topcoat only or ig inal L b 94.0 +0.1 92.6 +0.2 92.1 -0.1 91.9 -0.1 91.4 +0.1 9S.6 +0.2 91.2 +0.1 92.7 +0.1 Af ter 7 days at 105 0
C
L b 92.2 +0.3 90.4 +0.5 91.2 0 90.9 +0.3 90.4 +0.4 92.2 +0.5 90.5 +0.7 91.7 +0.5 Af ter 18 days at 105*C L b 91.6 +1.4 90.8 +1.3 90.9 91.5 90.2 +2.2 91.0 +42.2 90.9 +2.2 90.0 +1.9 9~ 4* '~4 a t .4 b 4 *4e a 4 44 *4# 93.3 +0.3 88.9 +3.6 89.3 +3.8 93.7 +0.4 89.0 +3.3 88.9 +3.6 t t t Ct e C t C
~K.
Claims (7)
- 7- The claims defining the invention are as follows: 1. A primer coating composition for cycloolefin polymer articles comprising: from 8% to 46% alkyd resin; from 3% to 18% urea- formaldehyde resin; from 25% to 83% of at least one 2-4 carbon alkanol; from 1.5% to 24% of nonleafing aluminium pigment; and from 0.5% to of an acid catalyst, based on the total weight of the composition. 2. The composition of claim 1 which additionally comprises from 2% to 22% of a cellulose ester and from 2.5% to 11% of a solvent for the cellulose ester, based on the total weight of the composition. 3. The composition of claim 2 wherein the cellulose ester is nitrocellulose. 4. The composition of any one of claims 1 to 3 wherein the alkanol is a mixture of ethanol and butanol. The composition of any one of claims 1 to 4 wherein the catalyst is para-toluenesulfonic acid. 0 6. The composition of any one of claims 1 to 5 wherein the S cycloolefin polymer is poly(dicyclopantadiene). o" 7. A process for preventing staining of painted cycloolefin polymer articles comprising applying a primer coating composition to the articles before painting, said composition comprising: from 8% to 46% alkyd resin; from 3% to 18% urea-formaldehyde resin; from 25% to 83% of at least one 2-4 carbon alkanol; from 1.5% to 24% of nonleafing aluminium pigment; and from 0.5% to 3.5% of an acid catalyst, based on the total weight of the composition and then causing the composition to 0000 080 cross-link before painting. :I r :R
- 8. The process of claim 7 wherein the S comprises from 2% to 22% of a cellulose ester solvent for the cellulose ester, based on the composition.
- 9. The process of claim 8 wherein the S' nitrocellulose. The process of any one of claims 7 mixture of ethanol and butanol.
- 11. The process of any one of claims 7 para-toluenesulfonic acid. composition additionally and from 2.5% to 11% of a total weight of the cellulose ester is to 9 wherein the alkanol is a to 10 wherein the catalyst is j i i dr .i iS i I q\p r g r~c. 8
- 12. The process of any one of claims 7 to 11 wherein the cycloolefin polymer is poly(dicyclopentadiene).
- 13. A primer coating composition for cycloolefin polymer articles subtiantially as hereinbefore described with reference to the Example.
- 14. A process for preventing staining of painted cycloolefin polymer articles substantially as hereinbefore described with reference to the Example. DATED this SECOND day of NOVEMBER 1989 Hercules Incorporated Patent Attorneys for the Applicant SPRUSON FERGUSON *0 *r, 0o 0 0~ *e S 8* 0 It Ct 00 I t a C O 4 ii I I r- Kt
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/884,821 US4710408A (en) | 1986-07-11 | 1986-07-11 | Primer coating for cycloolefin polymer articles |
| US884821 | 1986-07-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU7554387A AU7554387A (en) | 1988-01-14 |
| AU594796B2 true AU594796B2 (en) | 1990-03-15 |
Family
ID=25385472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU75543/87A Ceased AU594796B2 (en) | 1986-07-11 | 1987-07-10 | Primer for cycloolefin polymer articles |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4710408A (en) |
| EP (1) | EP0253301B1 (en) |
| JP (1) | JPS6323971A (en) |
| AU (1) | AU594796B2 (en) |
| BR (1) | BR8703547A (en) |
| CA (1) | CA1296118C (en) |
| DE (1) | DE3773559D1 (en) |
| ES (1) | ES2025103B3 (en) |
| ZA (1) | ZA875060B (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5716818A (en) * | 1981-04-25 | 1982-01-28 | Green Cross Corp:The | Steroid fatty emulsion |
| USD300265S (en) | 1986-05-28 | 1989-03-14 | Avon Products, Inc. | Design for cosmetic applicator |
| JPH01286812A (en) * | 1988-02-09 | 1989-11-17 | Nippon Zeon Co Ltd | Reaction injection molded product and its cutting processed product and their manufacture |
| US5169691A (en) * | 1988-09-06 | 1992-12-08 | Nippon Zeon Co., Ltd. | Coated polynorbornene product and method therefor |
| JPH0270431A (en) * | 1988-09-06 | 1990-03-09 | Nippon Zeon Co Ltd | Polynorbornene molded product and its manufacturing method |
| US5053256A (en) * | 1988-11-03 | 1991-10-01 | Hercules Incorporated | Sodium hypochlorite surface treatment to improve the adhesion of paints to polydicyclopentadiene |
| BR9007311A (en) * | 1989-04-20 | 1991-12-10 | Line Products Corp A | WATER COATING COMPOSITION |
| US5300363A (en) * | 1989-04-20 | 1994-04-05 | A-Line Products Corporation | Aqueous coating composition |
| US5756566A (en) * | 1989-04-20 | 1998-05-26 | A-Line Products Corp. | Aqueous coating composition |
| US5227198A (en) * | 1989-04-20 | 1993-07-13 | A-Line Products Corporation | Aqueous coating composition and method of use |
| JPH02305636A (en) * | 1989-05-19 | 1990-12-19 | Yamaha Motor Co Ltd | Resin structure |
| CA2112146A1 (en) * | 1992-12-23 | 1994-06-24 | Nitya P. Khasat | Polydicyclopentadiene having improved stability and toughened with polymeric particles |
| USH1388H (en) * | 1992-12-23 | 1994-12-06 | Hercules Incorporated | Polyolefin polymer and method of making same |
| US20050202263A1 (en) * | 2004-03-09 | 2005-09-15 | Jonathan Sargent | Barrier layer to prevent the loss of additives in an underlying layer |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1042897A (en) * | 1961-02-08 | 1966-09-14 | Ici Ltd | Coated films |
| EP0137256A2 (en) * | 1983-09-14 | 1985-04-17 | BASF Lacke + Farben AG | Coating mass, process for the preparation of coatings and coated substrate |
| US4532177A (en) * | 1984-04-02 | 1985-07-30 | Eastman Kodak Company | Base coat compositions for wet-on-wet applications, and articles coated therewith |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB482281A (en) * | 1936-09-22 | 1938-03-22 | Du Pont | Improvements in or relating to the production of resinous compositions |
| GB518309A (en) * | 1939-07-29 | 1940-02-22 | Lewis Berger & Sons Ltd | Improvements in or relating to synthetic metallic enamels |
| US4400340A (en) * | 1982-01-25 | 1983-08-23 | Hercules Incorporated | Method for making a dicyclopentadiene thermoset polymer |
| GB1284755A (en) * | 1968-09-30 | 1972-08-09 | Celanese Coatings Co | Process for coating surfaces and compositions for use therein |
| GB1435714A (en) * | 1972-06-05 | 1976-05-12 | Ici Ltd | Lacquer |
| JPS6044027B2 (en) * | 1977-06-14 | 1985-10-01 | 関西ペイント株式会社 | Metallic finishing method |
| US4218516A (en) * | 1979-01-26 | 1980-08-19 | The Dow Chemical Company | Pigment for blocking tannin migration |
| DE2938308C2 (en) * | 1979-09-21 | 1985-01-10 | Basf Farben + Fasern Ag, 2000 Hamburg | Substrate with curable or cured multi-layer paint, process for its production and use |
| US4391858A (en) * | 1981-11-20 | 1983-07-05 | Glasurit America, Inc. | Coating process |
| DE3151350A1 (en) * | 1981-12-24 | 1983-07-07 | Bayer Ag, 5090 Leverkusen | PLASTIC MOLDED BODIES EQUIPPED WITH A 3-LAYER COVER AND A METHOD FOR PRODUCING THE EQUIPMENT |
| JPS60122079A (en) * | 1983-12-02 | 1985-06-29 | Kansai Paint Co Ltd | Coating method |
-
1986
- 1986-07-11 US US06/884,821 patent/US4710408A/en not_active Expired - Fee Related
-
1987
- 1987-05-29 CA CA000538329A patent/CA1296118C/en not_active Expired - Fee Related
- 1987-07-08 DE DE8787109889T patent/DE3773559D1/en not_active Expired - Fee Related
- 1987-07-08 ES ES87109889T patent/ES2025103B3/en not_active Expired - Lifetime
- 1987-07-08 EP EP87109889A patent/EP0253301B1/en not_active Expired - Lifetime
- 1987-07-10 BR BR8703547A patent/BR8703547A/en unknown
- 1987-07-10 ZA ZA875060A patent/ZA875060B/en unknown
- 1987-07-10 JP JP62171326A patent/JPS6323971A/en active Pending
- 1987-07-10 AU AU75543/87A patent/AU594796B2/en not_active Ceased
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1042897A (en) * | 1961-02-08 | 1966-09-14 | Ici Ltd | Coated films |
| EP0137256A2 (en) * | 1983-09-14 | 1985-04-17 | BASF Lacke + Farben AG | Coating mass, process for the preparation of coatings and coated substrate |
| US4532177A (en) * | 1984-04-02 | 1985-07-30 | Eastman Kodak Company | Base coat compositions for wet-on-wet applications, and articles coated therewith |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0253301A2 (en) | 1988-01-20 |
| ZA875060B (en) | 1988-04-27 |
| BR8703547A (en) | 1988-03-22 |
| EP0253301A3 (en) | 1989-04-19 |
| EP0253301B1 (en) | 1991-10-09 |
| AU7554387A (en) | 1988-01-14 |
| JPS6323971A (en) | 1988-02-01 |
| ES2025103B3 (en) | 1992-03-16 |
| DE3773559D1 (en) | 1991-11-14 |
| US4710408A (en) | 1987-12-01 |
| CA1296118C (en) | 1992-02-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU594796B2 (en) | Primer for cycloolefin polymer articles | |
| US4598015A (en) | Multilayer satin finish automotive paint system | |
| US6596069B2 (en) | Glittering pigment and glittering coated film | |
| US5290543A (en) | Long wearing nail enamel topcoat and related methods | |
| AU648580B2 (en) | Non-metallic coating compositions containing very fine mica | |
| US2998324A (en) | Method of coating polypropylene | |
| US3429840A (en) | Acrylic resins containing cellulose butyrate benzoate,coatings and compositions | |
| US4283324A (en) | Nail enamel composition | |
| US4407990A (en) | Acrylic coating compositions | |
| US5520963A (en) | Paint formulation | |
| MXPA01008258A (en) | Method for producing two-layer final coats on motor vehicles. | |
| CA2119535C (en) | Water reducible polyester and resin composition for a flexible plastic primer | |
| US2866720A (en) | Decorative coating and method of making same | |
| JP3123697B2 (en) | Coating | |
| US5147453A (en) | Paint compositions containing silver metal flake pigment | |
| US5104915A (en) | Metal tinting lacquer composition | |
| US3634347A (en) | Acrylic lacquer coating composition containing a controlled quantity of low molecular weight melamine-formaldehyde resin | |
| US3036976A (en) | Coating composition comprising solvent, nitrocellulose and copolymer of methyl methacrylate with butoxyethyl methacrylate | |
| US20150328104A1 (en) | Novel photocrosslinkable compositions for use as base coat | |
| US2782132A (en) | Methyl methacrylate lacquer coated metal article and process therefor | |
| US3386941A (en) | Glass tinting lacquer compositions | |
| GB2123009A (en) | Light-stabilizing stoving finishes | |
| DE1163476B (en) | Sprayable paint | |
| US1564664A (en) | Film-forming composition | |
| CN109225784A (en) | A kind of paint application technique delaying timber paint layer aging |